Isopropyl chloroformate → Isopropyl 3,5-difluoro-phenylcarbamate

HRID 1179478Notes

Reaction equation

HRID 1179478 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[F:11][C:12]1[CH:13]=[C:14]([CH:16]=[C:17]([F:19])[CH:18]=1)[NH2:15].Cl[C:21]([O:23][CH:24]([CH3:26])[CH3:25])=[O:22]>C1COCC1.CCOCC>[F:11][C:12]1[CH:13]=[C:14]([NH:15][C:21](=[O:22])[O:23][CH:24]([CH3:26])[CH3:25])[CH:16]=[C:17]([F:19])[CH:18]=1

Participants

6

Reactant 3

HCID 7917Isopropyl chloroformateHCID 965953,5-DifluoroanilineHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 58978077Isopropyl 3,5-difluoro-phenylcarbamate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium bis(trimethylsilyl) amide (1.0 M solution in tetrahydrofuran, 542 mL, 0.542 mol) was added to a solution of 3,5-difluoroaniline (35 g, 0.271 mol) in THF (60 mL) at 0° C. Isopropyl chloroformate (1M solution in toluene, 406 mL, 0.406 mol) was then added dropwise at 0° C. and the mixture allowed to warm to room temperature over 2 h. The reaction mixture was diluted with ether and washed with 1N hydrochloric acid, water, saturated aqueous sodium bicarbonate, brine and dried (MgSO4). Solvent was removed under vacuum and the residue was triturated in hexanes to obtain the title compound.

Workup

  1. washwashed with 1N hydrochloric acid, water, saturated aqueous sodium bicarbonate, brine
  2. dry with materialdried (MgSO4)
  3. customSolvent was removed under vacuum
  4. customthe residue was triturated in hexanes

Sources & evidence

ORD record
ord-e00ebf9ef67c46d2949943269d0d0ab3
Source dataset
uspto-grants-2007_10
Patent number
US07279494B2

Reaction notes

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